NZ199360A - Phenylpyrimidines for protecting plants against phytotoxic damage - Google Patents

Phenylpyrimidines for protecting plants against phytotoxic damage

Info

Publication number: NZ199360A
Authority: NZ; New Zealand
Prior art keywords: herbicide; formula; phenylpyrimidine; seeds; halogen
Prior art date: 1980-12-23

Application number

NZ199360A

Other languages

English (en)

Inventor

K Burdeska

G Kabas

H-G Brunner

W Fory

Original Assignee

Ciba Geigy Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-12-23

Filing date

1981-12-22

Publication date

1986-04-11

1981-12-22 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1986-04-11 Publication of NZ199360A publication Critical patent/NZ199360A/en

Links

OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical class C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 title claims abstract description 61
230000000885 phytotoxic effect Effects 0.000 title claims abstract description 27
231100000208 phytotoxic Toxicity 0.000 title claims description 5
239000004009 herbicide Substances 0.000 claims abstract description 239
239000000729 antidote Substances 0.000 claims abstract description 158
229910052736 halogen Inorganic materials 0.000 claims abstract description 53
150000002367 halogens Chemical class 0.000 claims abstract description 53
-1 nitroanilides Chemical class 0.000 claims abstract description 42
239000002689 soil Substances 0.000 claims abstract description 34
239000000460 chlorine Substances 0.000 claims description 346
230000002363 herbicidal effect Effects 0.000 claims description 210
150000001875 compounds Chemical class 0.000 claims description 105
241000196324 Embryophyta Species 0.000 claims description 103
230000001681 protective effect Effects 0.000 claims description 99
239000000203 mixture Substances 0.000 claims description 84
238000000034 method Methods 0.000 claims description 75
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 62
235000007164 Oryza sativa Nutrition 0.000 claims description 57
235000009566 rice Nutrition 0.000 claims description 57
238000012360 testing method Methods 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 32
229910052739 hydrogen Inorganic materials 0.000 claims description 32
238000011156 evaluation Methods 0.000 claims description 28
229960001413 acetanilide Drugs 0.000 claims description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
150000002431 hydrogen Chemical class 0.000 claims description 18
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims description 16
240000006394 Sorghum bicolor Species 0.000 claims description 16
235000011684 Sorghum saccharatum Nutrition 0.000 claims description 16
240000008042 Zea mays Species 0.000 claims description 16
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 16
235000002017 Zea mays subsp mays Nutrition 0.000 claims description 16
235000009973 maize Nutrition 0.000 claims description 16
244000068988 Glycine max Species 0.000 claims description 15
235000010469 Glycine max Nutrition 0.000 claims description 15
235000013339 cereals Nutrition 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
150000003254 radicals Chemical class 0.000 claims description 14
BPEXTIMJLDWDTL-UHFFFAOYSA-N 2`-Methylacetanilide Chemical compound CC(=O)NC1=CC=CC=C1C BPEXTIMJLDWDTL-UHFFFAOYSA-N 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
239000011737 fluorine Substances 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
229920003023 plastic Polymers 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
239000004033 plastic Substances 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
239000011593 sulfur Substances 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 4
PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 4
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
239000011521 glass Substances 0.000 claims description 3
125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 claims description 3
WTDXDRUHQKVYKO-UHFFFAOYSA-N 4-hydroxy-2-phenyl-1h-pyrimidin-6-one Chemical compound OC1=CC(=O)NC(C=2C=CC=CC=2)=N1 WTDXDRUHQKVYKO-UHFFFAOYSA-N 0.000 claims description 2
230000001476 alcoholic effect Effects 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 2
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 2
SCCDDNKJYDZXMM-UHFFFAOYSA-N dimethachlor Chemical compound COCCN(C(=O)CCl)C1=C(C)C=CC=C1C SCCDDNKJYDZXMM-UHFFFAOYSA-N 0.000 claims description 2
230000002140 halogenating effect Effects 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000005499 phosphonyl group Chemical group 0.000 claims description 2
HVDCNOZINDETSA-UHFFFAOYSA-N sulfinylcarbamic acid Chemical compound OC(=O)N=S=O HVDCNOZINDETSA-UHFFFAOYSA-N 0.000 claims description 2
241000209094 Oryza Species 0.000 claims 28
241000209510 Liliopsida Species 0.000 claims 19
241001233957 eudicotyledons Species 0.000 claims 19
KTFNPLHWDYECSQ-UHFFFAOYSA-N 2-chloro-n-(ethoxymethyl)-n-[2-methyl-6-(trifluoromethyl)phenyl]acetamide Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1C(F)(F)F KTFNPLHWDYECSQ-UHFFFAOYSA-N 0.000 claims 6
244000045561 useful plants Species 0.000 claims 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 2
AFINAILKDBCXMX-PBHICJAKSA-N (2s,3r)-2-amino-3-hydroxy-n-(4-octylphenyl)butanamide Chemical compound CCCCCCCCC1=CC=C(NC(=O)[C@@H](N)[C@@H](C)O)C=C1 AFINAILKDBCXMX-PBHICJAKSA-N 0.000 claims 1
KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims 1
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
XVIRIXVOLLJIPF-UHFFFAOYSA-N 1-nitro-2-(2-nitrophenoxy)benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1OC1=CC=CC=C1[N+]([O-])=O XVIRIXVOLLJIPF-UHFFFAOYSA-N 0.000 claims 1
QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 claims 1
IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims 1
JIYYBQNJKKLWTP-UHFFFAOYSA-N 2-(4-bromophenyl)-4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC(C=2C=CC(Br)=CC=2)=N1 JIYYBQNJKKLWTP-UHFFFAOYSA-N 0.000 claims 1
JXTXGAQZMPFPOW-UHFFFAOYSA-N 4,6-dibromo-2-(4-methylphenyl)pyrimidine Chemical compound C1=CC(C)=CC=C1C1=NC(Br)=CC(Br)=N1 JXTXGAQZMPFPOW-UHFFFAOYSA-N 0.000 claims 1
SRTVVSLQGMWIAH-UHFFFAOYSA-N 4,6-dibromo-2-phenylpyrimidine Chemical compound BrC1=CC(Br)=NC(C=2C=CC=CC=2)=N1 SRTVVSLQGMWIAH-UHFFFAOYSA-N 0.000 claims 1
GDJGWGCBZULKBA-UHFFFAOYSA-N 4,6-dichloro-2-(2-methylphenyl)pyrimidine Chemical compound CC1=CC=CC=C1C1=NC(Cl)=CC(Cl)=N1 GDJGWGCBZULKBA-UHFFFAOYSA-N 0.000 claims 1
ZCESWQXDKHQLOD-UHFFFAOYSA-N 4,6-dichloro-2-(3,5-dimethoxyphenyl)pyrimidine Chemical compound COC1=CC(OC)=CC(C=2N=C(Cl)C=C(Cl)N=2)=C1 ZCESWQXDKHQLOD-UHFFFAOYSA-N 0.000 claims 1
NYZJGHDZMVCSPC-UHFFFAOYSA-N 4,6-dichloro-2-(3-methoxyphenyl)pyrimidine Chemical compound COC1=CC=CC(C=2N=C(Cl)C=C(Cl)N=2)=C1 NYZJGHDZMVCSPC-UHFFFAOYSA-N 0.000 claims 1
UIYGBIMLYLGCSI-UHFFFAOYSA-N 4,6-difluoro-2-phenylpyrimidine Chemical compound FC1=CC(F)=NC(C=2C=CC=CC=2)=N1 UIYGBIMLYLGCSI-UHFFFAOYSA-N 0.000 claims 1
DSSPSVOGHYUIPW-UHFFFAOYSA-N 4-(4,6-dichloropyrimidin-2-yl)phenol Chemical compound OC1=CC=C(C=C1)C1=NC(=CC(=N1)Cl)Cl DSSPSVOGHYUIPW-UHFFFAOYSA-N 0.000 claims 1
FTNZEMPDCJGRNQ-UHFFFAOYSA-N 4-chloro-2-(4-chlorophenyl)-6-fluoropyrimidine Chemical compound FC1=CC(Cl)=NC(C=2C=CC(Cl)=CC=2)=N1 FTNZEMPDCJGRNQ-UHFFFAOYSA-N 0.000 claims 1
OODVXBLXOCTTNZ-UHFFFAOYSA-N COCl.[F] Chemical compound COCl.[F] OODVXBLXOCTTNZ-UHFFFAOYSA-N 0.000 claims 1
IPASTOLBLUFKSI-UHFFFAOYSA-N ClC1=CC(Cl)=NC(C=2C=CC(=CC=2)C#C)=N1 Chemical compound ClC1=CC(Cl)=NC(C=2C=CC(=CC=2)C#C)=N1 IPASTOLBLUFKSI-UHFFFAOYSA-N 0.000 claims 1
102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 1
101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims 1
101150052863 THY1 gene Proteins 0.000 claims 1
GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
229940075522 antidotes Drugs 0.000 abstract description 9
239000002253 acid Substances 0.000 abstract description 5
150000004657 carbamic acid derivatives Chemical class 0.000 abstract description 5
150000003558 thiocarbamic acid derivatives Chemical class 0.000 abstract description 5
150000001558 benzoic acid derivatives Chemical class 0.000 abstract description 4
150000003918 triazines Chemical class 0.000 abstract description 4
150000007513 acids Chemical class 0.000 abstract description 2
240000007594 Oryza sativa Species 0.000 description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
239000000243 solution Substances 0.000 description 33
UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000004480 active ingredient Substances 0.000 description 14
238000002054 transplantation Methods 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
239000000126 substance Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 9
HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 9
125000001309 chloro group Chemical group Cl* 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
238000009331 sowing Methods 0.000 description 9
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
238000009472 formulation Methods 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
229920000151 polyglycol Polymers 0.000 description 8
239000010695 polyglycol Substances 0.000 description 8
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 8
QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 description 7
241000209140 Triticum Species 0.000 description 7
235000021307 Triticum Nutrition 0.000 description 7
235000019441 ethanol Nutrition 0.000 description 7
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 7
DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 7
239000007787 solid Substances 0.000 description 7
239000004094 surface-active agent Substances 0.000 description 7
YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
239000005995 Aluminium silicate Substances 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 6
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 6
235000012211 aluminium silicate Nutrition 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
239000000843 powder Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000002202 Polyethylene glycol Substances 0.000 description 5
239000000969 carrier Substances 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 5
235000021186 dishes Nutrition 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
239000002736 nonionic surfactant Substances 0.000 description 5
229920001223 polyethylene glycol Polymers 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
NBMZAZJUGREBFI-UHFFFAOYSA-N 2-(4-methylphenyl)-4,6-di(propan-2-yloxy)pyrimidine Chemical compound CC(C)OC1=CC(OC(C)C)=NC(C=2C=CC(C)=CC=2)=N1 NBMZAZJUGREBFI-UHFFFAOYSA-N 0.000 description 4
SPGOAFUOMCIVDB-UHFFFAOYSA-N 4,6-dichloro-2-(4-methylphenyl)pyrimidine Chemical compound C1=CC(C)=CC=C1C1=NC(Cl)=CC(Cl)=N1 SPGOAFUOMCIVDB-UHFFFAOYSA-N 0.000 description 4
VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 4
240000005979 Hordeum vulgare Species 0.000 description 4
235000007340 Hordeum vulgare Nutrition 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
229910019142 PO4 Inorganic materials 0.000 description 4
UNLYSVIDNRIVFJ-UHFFFAOYSA-N Piperophos Chemical compound CCCOP(=S)(OCCC)SCC(=O)N1CCCCC1C UNLYSVIDNRIVFJ-UHFFFAOYSA-N 0.000 description 4
239000002671 adjuvant Substances 0.000 description 4
239000003905 agrochemical Substances 0.000 description 4
235000019993 champagne Nutrition 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
235000015097 nutrients Nutrition 0.000 description 4
235000021317 phosphate Nutrition 0.000 description 4
150000003013 phosphoric acid derivatives Chemical class 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
235000015112 vegetable and seed oil Nutrition 0.000 description 4
239000008158 vegetable oil Substances 0.000 description 4
HOTSOIAAMTWIGO-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-hydroxy-1h-pyrimidin-6-one Chemical compound OC1=CC(O)=NC(C=2C=CC(Cl)=CC=2)=N1 HOTSOIAAMTWIGO-UHFFFAOYSA-N 0.000 description 3
VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
SPANOECCGNXGNR-UITAMQMPSA-N Diallat Chemical compound CC(C)N(C(C)C)C(=O)SC\C(Cl)=C\Cl SPANOECCGNXGNR-UITAMQMPSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 description 1
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SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
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239000003760 tallow Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3

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Zoology (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
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Agricultural Chemicals And Associated Chemicals (AREA)
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Medicines Containing Plant Substances (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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Treatment Of Liquids With Adsorbents In General (AREA)
Catching Or Destruction (AREA)
Liquid Crystal Substances (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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NZ199360A 1980-12-23 1981-12-22 Phenylpyrimidines for protecting plants against phytotoxic damage NZ199360A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH952280		1980-12-23
CH236381		1981-04-08

Publications (1)

Publication Number	Publication Date
NZ199360A true NZ199360A (en)	1986-04-11

Family

ID=25690262

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NZ199360A NZ199360A (en)	1980-12-23	1981-12-22	Phenylpyrimidines for protecting plants against phytotoxic damage

Country Status (30)

Country	Link
US (2)	US4493726A (xx)
EP (1)	EP0055693B1 (xx)
KR (1)	KR890001062B1 (xx)
AT (1)	ATE32065T1 (xx)
AU (1)	AU558710B2 (xx)
BG (1)	BG37221A3 (xx)
BR (1)	BR8108383A (xx)
CA (1)	CA1220953A (xx)
CS (1)	CS243465B2 (xx)
DD (1)	DD202798A5 (xx)
DE (1)	DE3176621D1 (xx)
DK (1)	DK156687C (xx)
DO (1)	DOP1981004033A (xx)
ES (1)	ES508254A0 (xx)
GR (1)	GR76379B (xx)
HU (1)	HU191339B (xx)
IL (1)	IL64612A (xx)
IN (1)	IN159209B (xx)
MA (1)	MA19355A1 (xx)
MX (1)	MX6720E (xx)
MY (1)	MY101392A (xx)
NZ (1)	NZ199360A (xx)
OA (1)	OA06972A (xx)
PH (1)	PH19369A (xx)
PL (1)	PL130575B1 (xx)
PT (1)	PT74181B (xx)
RO (1)	RO83451B (xx)
SU (1)	SU1482505A3 (xx)
YU (1)	YU43250B (xx)
ZW (1)	ZW30681A1 (xx)

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- 1981-12-16 MX MX819839U patent/MX6720E/es unknown
- 1981-12-17 EP EP81810505A patent/EP0055693B1/de not_active Expired
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- 1981-12-21 PH PH26661A patent/PH19369A/en unknown
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- 1981-12-21 IL IL64612A patent/IL64612A/xx not_active IP Right Cessation
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- 1981-12-22 DK DK571281A patent/DK156687C/da active
- 1981-12-22 ES ES508254A patent/ES508254A0/es active Granted
- 1981-12-22 PT PT74181A patent/PT74181B/pt not_active IP Right Cessation
- 1981-12-22 HU HU813912A patent/HU191339B/hu unknown
- 1981-12-22 DD DD81236096A patent/DD202798A5/de not_active IP Right Cessation
- 1981-12-22 CS CS819672A patent/CS243465B2/cs unknown
- 1981-12-22 NZ NZ199360A patent/NZ199360A/en unknown
- 1981-12-22 SU SU813369450A patent/SU1482505A3/ru active
- 1981-12-22 YU YU3058/81A patent/YU43250B/xx unknown
- 1981-12-22 BG BG054640A patent/BG37221A3/xx unknown
- 1981-12-23 PL PL1981234418A patent/PL130575B1/pl unknown
- 1981-12-23 RO RO106092A patent/RO83451B/ro unknown
- 1981-12-23 AU AU78840/81A patent/AU558710B2/en not_active Ceased
- 1981-12-23 BR BR8108383A patent/BR8108383A/pt unknown
- 1981-12-23 OA OA57573A patent/OA06972A/xx unknown
- 1981-12-23 KR KR1019810005105A patent/KR890001062B1/ko not_active IP Right Cessation
1983
- 1983-04-20 US US06/486,651 patent/US4493726A/en not_active Expired - Lifetime
1984
- 1984-11-02 US US06/667,705 patent/US4674229A/en not_active Expired - Lifetime
1987
- 1987-10-01 MY MYPI87002826A patent/MY101392A/en unknown

Also Published As

Publication number	Publication date
YU43250B (en)	1989-06-30
US4674229A (en)	1987-06-23
AU558710B2 (en)	1987-02-05
ES8300322A1 (es)	1982-11-01
DE3176621D1 (en)	1988-02-25
PL234418A1 (xx)	1982-08-02
ES508254A0 (es)	1982-11-01
PT74181A (pt)	1982-01-02
RO83451A (ro)	1984-02-21
CA1220953A (en)	1987-04-28
IN159209B (xx)	1987-04-11
DD202798A5 (de)	1983-10-05
YU305881A (en)	1984-04-30
EP0055693B1 (de)	1988-01-20
KR830006896A (ko)	1983-10-12
IL64612A (en)	1988-09-30
DK156687B (da)	1989-09-25
MA19355A1 (fr)	1982-07-01
ATE32065T1 (de)	1988-02-15
US4493726A (en)	1985-01-15
OA06972A (fr)	1983-07-31
GR76379B (xx)	1984-08-06
RO83451B (ro)	1984-02-28
KR890001062B1 (ko)	1989-04-22
HU191339B (en)	1987-02-27
PT74181B (pt)	1985-01-04
DK156687C (da)	1990-03-12
MX6720E (es)	1985-11-07
PH19369A (en)	1986-04-02
DK571281A (da)	1982-06-24
CS243465B2 (en)	1986-06-12
AU7884081A (en)	1982-07-01
CS967281A2 (en)	1985-08-15
BG37221A3 (en)	1985-04-15
BR8108383A (pt)	1982-10-13
ZW30681A1 (en)	1982-07-14
SU1482505A3 (ru)	1989-05-23
DOP1981004033A (es)	1990-12-29
MY101392A (en)	1991-10-23
IL64612A0 (en)	1982-03-31
EP0055693A1 (de)	1982-07-07
PL130575B1 (en)	1984-08-31

Publication	Publication Date	Title
NZ199360A (en)	1986-04-11	Phenylpyrimidines for protecting plants against phytotoxic damage
KR100320168B1 (ko)	2002-11-23	치환된(헤테로)아릴화합물,이의제조방법,이를함유한물질,및독성완화제로서의용도
CA1218994A (en)	1987-03-10	Use of quinoline derivatives for the protection of cultivated plants
US4698091A (en)	1987-10-06	2-phenylpyrimidines, 2-naphthylpyrimidines and 2-heterocyclylpyrimidines as safeners for protecting cultivated plant against phytotoxic damage caused by herbicides
JPS63115870A (ja)	1988-05-20	２−フエノキシピリミジン誘導体および除草剤
JPH026477A (ja)	1990-01-10	除草性および植物生長調節性を有するｎ―フェニル―ｎ―ピリミジン―２―イル尿素
CA1278695C (en)	1991-01-08	Herbicidal composition
JP3148007B2 (ja)	2001-03-19	サリチル（チオ）エーテル誘導体、これを含有する除草剤およびこれを製造するための中間生成物
CA2007351A1 (en)	1990-07-11	Antidotes for improving the tolerance of cultivated plants towards agrochemical active substances
SK11792001A3 (sk)	2002-01-07	1-Aryl-1,3,5-triazín-4-tión-2,6-dióny, ich príprava a ich použitie ako herbicídov
CA1233819A (en)	1988-03-08	2-aryl-4,6-dihalopyrimidines as antidote for protecting cultivated plants from phytotoxic damage caused by herbicides
US5108482A (en)	1992-04-28	N-phenylpyrrolidines
JPH0253402B2 (xx)	1990-11-16
US5188657A (en)	1993-02-23	Herbicidal sulfonylureas and their use
CA1200248A (en)	1986-02-04	Cyclopropanecarboxylic acid derivatives
US4483707A (en)	1984-11-20	Phenylamino-oxo-acetic acids and esters thereof as antidotes for protecting cultivated plants from the phytotoxic action of aggressive herbicides
AU616191B2 (en)	1991-10-24	Heterocyclic-substituted phenylsulfamates, processes for their preparation and their use as herbicides and plant growth regulators
US5362876A (en)	1994-11-08	Salicylaldehyde and salicylic acid derivatives and sulfur analogs thereof, their preparation and intermediates therefor
US5162537A (en)	1992-11-10	Benzhydryl compounds as herbicide antidotes
US4605764A (en)	1986-08-12	Substituted acetamide derivatives with an antidote action, antidote compositions containing such compounds, selective herbicide compositions containing these antidotes and a process for the preparation of substituted acetamide derivatives
JPS59222442A (ja)	1984-12-14	光学活性なプロピオン酸エステル誘導体
NL8201783A (nl)	1982-11-16	Fenoxybenzoezuurderivaten, hun bereiding en hun gebruik voor de selektieve onkruidbestrijding in kulturen.
JPS6041066B2 (ja)	1985-09-13	ベンズオキサゾロン誘導体及びそれを含有する農園芸用殺菌剤
JPH037284A (ja)	1991-01-14	スルタムスルホンアミド誘導体及び除草剤
CS246333B1 (en)	1986-10-16	2-(aryloxyacetyloxy) phthalimides